View 14531 CEDAR HILL DRIVE Winter Garden, FL MLS# O6408070
  • Recently Listed with Virtual Tour
1 of 51
$749,000
5

Beds

4.0

Baths

3,510

Sq.Ft.

14531 CEDAR HILL DRIVE

Winter Garden, FL

Courtesy of REAL BROKER, LLC
View 8866 BISMARCK PALM DRIVE Winter Garden, FL MLS# O6408155
  • Recently Listed with Virtual Tour
1 of 64
$795,000
5

Beds

4.0

Baths

3,174

Sq.Ft.

8866 BISMARCK PALM DRIVE

Winter Garden, FL

Courtesy of EXP REALTY LLC
View 907 EASLEY AVENUE Winter Garden, FL MLS# O6406147
  • Recently Listed
1 of 67
$865,000
3

Beds

2.1

Baths

2,252

Sq.Ft.

907 EASLEY AVENUE

Winter Garden, FL

Courtesy of BHHS FLORIDA REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 7549 SPRING VALLEY STREET Winter Garden, FL MLS# G5112279
$730,791
4

Beds

3.1

Baths

2,515

Sq.Ft.

7549 SPRING VALLEY STREET

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 17422 SUNSET PRAIRIE DRIVE Winter Garden, FL MLS# G5112284
$671,415
4

Beds

2.1

Baths

2,235

Sq.Ft.

17422 SUNSET PRAIRIE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 708 ORANGE BELT LOOP Winter Garden, FL MLS# G5112211
  • Recently Listed with Virtual Tour
1 of 46
$745,000
3

Beds

2.0

Baths

1,916

Sq.Ft.

708 ORANGE BELT LOOP

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 5978 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112233
  • Recently Listed with Virtual Tour
1 of 5
$681,240
4

Beds

2.1

Baths

2,802

Sq.Ft.

5978 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 7922 WINTER WREN STREET Winter Garden, FL MLS# O6406681
  • Recently Listed with Virtual Tour
1 of 53
$765,900
4

Beds

3.1

Baths

3,391

Sq.Ft.

7922 WINTER WREN STREET

Winter Garden, FL

Courtesy of YORK MILLS REALTY LLC
View 15232 FIRELIGHT DRIVE Winter Garden, FL MLS# O6408025
  • Recently Listed with Virtual Tour
1 of 64
$829,000
7

Beds

4.0

Baths

4,612

Sq.Ft.

15232 FIRELIGHT DRIVE

Winter Garden, FL

Courtesy of CORCORAN PREMIER REALTY
View 6153 FLOWERING CHERRY BEND Winter Garden, FL MLS# G5112171
$680,030
4

Beds

2.1

Baths

2,235

Sq.Ft.

6153 FLOWERING CHERRY BEND

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 921 Westcliffe Drive Winter Garden, FL MLS# B26027811
  • Recently Listed with Virtual Tour
1 of 16
OPEN HOUSE: Saturday 5/30 10:00 AM - 2:00 PM
$750,000
4

Beds

2.1

Baths

2,354

Sq.Ft.

921 Westcliffe Drive

Winter Garden, FL

View 15081 TEA TREE DRIVE Winter Garden, FL MLS# G5112081
  • New Construction with Virtual Tour
1 of 47
$797,398
4

Beds

3.1

Baths

2,688

Sq.Ft.

15081 TEA TREE DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11265 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405351
  • New Construction with Virtual Tour
1 of 7
$870,331
5

Beds

4.1

Baths

3,225

Sq.Ft.

11265 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13410 PEACEFULL MELODY DRIVE Winter Garden, FL MLS# G5112004
  • New Construction with Virtual Tour
1 of 26
$794,990
5

Beds

3.1

Baths

3,076

Sq.Ft.

13410 PEACEFULL MELODY DRIVE

Winter Garden, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 11253 HOLLOW BAY DRIVE Winter Garden, FL MLS# O6405126
  • New Construction with Virtual Tour
1 of 18
$819,106
4

Beds

3.0

Baths

2,113

Sq.Ft.

11253 HOLLOW BAY DRIVE

Winter Garden, FL

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC
View 13728 FOX GLOVE STREET Winter Garden, FL MLS# O6405142
  • Recently Listed with Virtual Tour
1 of 37
$719,900
5

Beds

3.1

Baths

3,391

Sq.Ft.

13728 FOX GLOVE STREET

Winter Garden, FL

Courtesy of CRYSTAL CLEAR REALTY LLC
View 931 KYLEE ALLEY Winter Garden, FL MLS# O6404673
$775,000
4

Beds

4.0

Baths

2,831

Sq.Ft.

931 KYLEE ALLEY

Winter Garden, FL

Courtesy of COMPASS FLORIDA LLC
View 10187 MERRYMEETING BAY DRIVE Winter Garden, FL MLS# O6404599
$679,000
4

Beds

3.1

Baths

2,840

Sq.Ft.

10187 MERRYMEETING BAY DRIVE

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 5139 LAKE HAMLIN TRAIL Winter Garden, FL MLS# O6404614
  • Recently Listed with Virtual Tour
1 of 41
$675,000
4

Beds

2.1

Baths

2,742

Sq.Ft.

5139 LAKE HAMLIN TRAIL

Winter Garden, FL

Courtesy of SPRING REALTY ONE LLC
View 8721 BAYVIEW CROSSING DRIVE Winter Garden, FL MLS# G5111855
$695,000
4

Beds

3.1

Baths

2,842

Sq.Ft.

8721 BAYVIEW CROSSING DRIVE

Winter Garden, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY

About Winter Garden

The balance between reverence for yesterday and vibrant growth is reflected in the Winter Garden slogan, "A City with a Future…Preserving Its Past."  Walking down historic Plant Street or catching a glimpse of landmark buildings like Tanner Hall immediately creates an image of small-town life at its finest in the heart of this quaint Main Street community. At the same time, redevelopment and growth are evident at every turn.  Antique stores, ice cream shops, and charming cafés combine with dynamic new businesses and residential development.  Covering approximately 17 square miles, Winter Garden offers access to the West Orange Trail for biking or jogging in a naturally beautiful setting.  Other amenities include large parks, a public boat ramp on Lake Apopka, and recreational complexes for tennis, swimming, and sports play.  This vast area once covered by citrus groves is rapidly transforming into a suburban environment that preserves the friendly, intimate spirit of yesterday.  Residents enjoy easy access to Highway 50, the East West Expressway, and the Florida Turnpike.

Listings in Winter Garden, FL

1,045

Estimated median home price

$609,000
Winter Garden FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Garden, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Garden, FL.

Homes for Sale by Price in Winter Garden, FL

PriceCount
$0 - 100K2
$100K - 200K23
$200K - 300K97
$300K - 400K83
$400K - 500K143
$500K - 600K171
$600K - 700K124
$700K - 800K118
$800K - 900K86
$900K - 1M73
$1M - Max125

Homes for Sale by Type in Winter Garden, FL

Property TypeCount
Single Family717
Townhouse142
Condo144
Commercial10
Rental216
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home2
Farms0

(Data as of 5/27/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 5/27/2026.